Method for synthesizing 3-hydroxy-azetidinehydrochloride

A technique for the synthesis of azetidine, which is applied in the field of compound preparation, and can solve the problems of expensive benzhydrylamine, high energy consumption, and long reaction time, etc.

Inactive Publication Date: 2012-12-19
甘肃科瑞生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Wherein the reaction time of the first step is very long, needs to react about 6 days, and energy consumption is too high, and benzhydrylamine is more expensive, and this has brought very big resistance to the industrialization of this product, and the removal of benzhydryl is also difficult. Difficult, long reaction time

Method used

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  • Method for synthesizing 3-hydroxy-azetidinehydrochloride
  • Method for synthesizing 3-hydroxy-azetidinehydrochloride
  • Method for synthesizing 3-hydroxy-azetidinehydrochloride

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Embodiment 1

[0029] The synthetic method of 3-hydroxyl-azetidine hydrochloride, comprises the following steps:

[0030] (1) Dissolve benzylamine in 15 times the mass of water, cool down to 0-5°C, slowly add epichlorohydrin (1.3 equivalents) to the above reaction solution, maintain the system at 0-5°C, and react for 12 hours. GC monitoring raw material reaction is complete. Filter, wash the filter cake twice with 2 times the mass of water, and then wash once with an organic solvent with a volume ratio of 2 times the mass of ethyl acetate:petroleum ether=1:20. Let it dry to get the product of the first step. HPLC detection, purity greater than 96%, used directly for the next step. Yield 89%.

[0031] (2) Dissolve the compound prepared in the first step in 15 times the mass of acetonitrile, add 1.5 equivalents of sodium carbonate, and heat the reaction system to reflux. The reaction was carried out for 12 hours, and the reaction of the raw materials was detected by HPLC. After cooling an...

Embodiment 2

[0034] The synthetic method of 3-hydroxyl-azetidine hydrochloride, comprises the following steps:

[0035] (1) Dissolve 1 kg of benzylamine in 15 kg of water, cool down to 0°C, slowly add 1.117 kg of epichlorohydrin to the above reaction solution, keep the system not exceeding 5°C during the whole addition process, stir and maintain At this temperature, react for 12 hours, HPLC detects that benzylamine has reacted completely, return to room temperature, filter the reaction solution, wash the filter cake twice with 2 kg of water, and then use 2 kg of ethyl acetate:petroleum ether=1 : 20% organic solvent washing, product dries, obtains 1649 grams of product, HPLC detects purity 96.7%, yield 88.7%

[0036] (2) Dissolve 1649 grams of the compound obtained in the first step in 25 kilograms of acetonitrile, add 878 grams of sodium carbonate, then heat to reflux, react for 12 hours, and detect by HPLC, the reaction of the raw materials is complete,

[0037] Cooled to room temperatur...

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Abstract

The invention discloses a method for synthesizing 3-hydroxy-azetidinehydrochloride, which comprises the following steps: (1) preparing an intermediate product; (2) preparing 1-benzyl-3hydroxyazetidine; and (3) preparing a final product. According to the invention, the method disclosed by the invention has advantages of a short production period, high yield and low energy consumption.

Description

technical field [0001] The invention relates to a preparation method of a compound, in particular to a synthesis method of 3-hydroxy-azetidine hydrochloride. Background technique [0002] 3-hydroxyl-azetidine hydrochloride is a very useful pharmaceutical intermediate, but the current domestic method for synthesizing 3-hydroxyl-azetidine hydrochloride is to use epichlorohydrin as a raw material. Open the ring with benzhydrylamine, then close the ring, and remove the benzhydryl group with palladium carbon. Wherein the reaction time of the first step is very long, needs to react about 6 days, and energy consumption is too high, and benzhydrylamine is more expensive, and this has brought very big resistance to the industrialization of this product, and the removal of benzhydryl is also difficult. Difficult and takes a long time to react. Contents of the invention [0003] The technical problem to be solved by the present invention is to overcome existing defects and provide ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D205/04
Inventor 詹智年
Owner 甘肃科瑞生物科技有限公司
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